The only-in-NY trial that brings together a lawyer to drug kingpins, his mob attorney, and the Gotti prosecutor

As for Simels? "He is willing to do things that lawyers shouldn't do on behalf of their clients," says a former prosecutor and adversary of Simels who declines to be named. "Some attorneys go beyond being advocates and become part of the organization, which is unfortunate because Simels is a competent lawyer, but he definitely crosses the line. I've seen enough of Bob Simels that it does not surprise me that his name has come up as someone who would be in this kind of trouble."

Not so, says Shargel.

Concerning the affidavit and other contentions by prosecutors, Shargel calls the conversations on the tapes "a cat and mouse game," in which ambiguous conversations "dangle in mid-air" and, besides, contain material that is "profoundly helpful" to his defense of Simels.

Shargel won't directly touch the topic of whether the prosecution of Simels's conduct is punitive, saying only, "I have my own private thoughts on the motive for sending in a . . . wired cooperator on very scant evidence of anything."

The allegations contained in the government's indictment of Bob Simels are similar to allegations that have dogged him for years, particularly those levied against him during the 1988 trial of accused drug kingpin Brooks Davis.

During that trial, court documents show, Simels paid a visit to a witness, who had confessed to the government his involvement in the attempted murder of a witness against Davis. When Davis and the cooperating witness were mistakenly put into the same holding cell in the Metropolitan Correctional Center, Davis allegedly told the witness that he would send his lawyer, Simels, to see him. According to court documents, "the purpose of the lawyer's visit was for [the witness] to sign a paper stating that he 'ain't going to testify.' "

Two days later, Simels presented an affidavit from the informant that said his previous statements to the government about Davis were false. The government then presented evidence stating that, during his visit with the informant at MCC, Simels warned the informant that "he should not testify against his 'friends' from the 'street,' while [his] family [was] out there." A mistrial was declared as the specter of Simels's becoming a witness in the trial loomed.

You almost have to think that Bob Simels would know better than to get himself in this kind of trouble. He began his career in the early '70s in the New York State Special Prosecutor's Office, where he worked on the prosecution of corruption cases involving links between the NYPD and organized crime.

Simels has told Pileggi that, upon entering private practice in the late '70s, he had always wanted to be a mob lawyer, but because of his association with Hill, who was considered a "rat," Italian gangsters sought to distance themselves from him. Simels wound up representing drug kingpins who have become street legends, such as "Boy George" Rivera, who, by the time he was arrested at 21, according to the feds, had amassed some $15 million from his "Obsession" brand of heroin. (In 1991, Rivera received a life sentence without parole.) Another of Simels's clients, Thomas "Tony Montana" Mickens, was known for his profligate spending, acumen as a money launderer, and obsessive admiration for Al Pacino's Scarface character. He is now serving a 35-year sentence.

Another of Simels's clients was Lorenzo "Fat Cat" Nichols, the Jamaica, Queens, drug gang leader now serving a life sentence on narcotics charges and an additional 40-year sentence for the 1985 murder of his parole officer. It was Nichols's associate, Howard "Pappy" Mason, who was convicted in the murder of rookie police officer Edward Byrne, a killing that brought a new level of law enforcement scrutiny and public attention to the kingpins, and signaled the beginning of the end of their reign.

Of Simels's kingpin clients, perhaps none is more notorious than Kenneth "Supreme" McGriff, who, along with his violent "Supreme Team" drug gang, turned South Jamaica Queens' Baisley housing projects into what is said to be one of the models for the Carter, the enormous crackhouse/storehouse in the movie New Jack City. McGriff's stature in southeast Queens—along with romanticized notions about his influence there—have made him a point of reference for many rappers. (Indeed, it was 50 Cent's detailed description of the Supreme Team organization's machinations in his song "Ghetto Qu'ran" that, prevailing street wisdom has it, led to his being shot nine times during a 2000 attempt on his life.) In 1989, under Simels's counsel, McGriff pleaded guilty to drug charges and served the better part of eight years behind bars (he had been facing 150 years). In 2005, he was charged, along with Irv and Chris Gotti, née Lorenzo, with laundering Supreme Team drug money through the rap label Murder, Inc., which was headed by Irv Lorenzo. Their case was ultimately separated from that of McGriff, and the Lorenzos, with Gerald Shargel as part of their defense team, were eventually acquitted. McGriff was charged with ordering the murder of two rivals in 2001 and is serving a life sentence. (Simels also defended former Jets Ken O'Brien and Marc Gastineau to satisfaction in their respective assault charges in the '80s; O'Brien's stemmed from a Studio 54 brawl, Gastineau's from a domestic incident.)